11 Best Vintage Rolex Watches To Enhance Your Style

Rolex is one of the most iconic premium watch brands in the world. If you get a brand new Rolex watch today, then you’re likely going to need to spend a fortune, especially for the most gorgeous models they have available.

However, with so much brand history, there are a lot of chances for you to pick up some vintage watches that can fit with any outfit you’re looking to create.

11 Best Vintage Rolex Watches To Enhance Your Style

So then, if you’re considering picking up some vintage Rolex watches to enhance your style, you’ve come to the right article!

In the sections below, we’re going to take you through a list of the best vintage pieces we could find, breaking down each one for you.

We’ve also made sure to include a short FAQ section that will help explain anything else you might need to know about Rolex watches.

History Of Rolex 

Rolex was created in 1905 by Hans Wilsdorf and Alfred Davis in London. The company initially imported Swiss movements, placing them into watch cases made by Dennison and other manufacturers.

In 1910,  Rolex began to create its own. During this time period, Rolex achieved the first ever Swiss Chronometer certification for a wristwatch, which was an impressive accomplishment at the time.

Throughout the rest of the 20th century, Rolex expanded to innovate on its designs and became renowned for making iconic watches.

Some of their most iconic ranges throughout this time included the Submariner, GMT-Master, and Daytona. Today, Rolex is considered one of the most prestigious and respected, premium watch brands in the world.

Rolex is often used synonymously for luxury when it comes to watches. 

The 11 Best Vintage Rolex Watches 


1. Rolex Cosmograph Daytona “Paul Newman”

The “Paul Newman” Daytona is one of the most iconic pieces in Rolex’s long and storied range.

Given their name by the actor Paul Newman (who owned one himself), these watches are highly sought after, and distinct from a standard Daytona watch because of their unique, vintage dial. 

Notice here the three distinct dials on the Paul Newman watch that were created by Singer—these are the defining feature of this vintage watch that create a unique and distinctly 60s/70s look.

Paul Newman Daytonas are extremely up-market and rare, and you can expect to find one for anywhere up to over six figures if you want to pick one up. 


2. Rolex Explorer (Ref. 1016)

Next up, we have what might be one of the most simplistic-looking watches on this list. It includes an understated dial that simply tells the time with no additional features.

What makes this watch special is its important history in relation to exploration and important expeditions during the 1950s.

 In 1953, Sir Edmund Hillary and Tenzing Norgay were the first people to summit mount Everest, an iconic moment for explorers worldwide.

Rolex used this moment to market this watch, stating that Sir Edmund wore this watch on his ascent. Although in truth he actually wore an older prototype version, this clever marketing added to the overall mystique and status of this watch. 

In comparison to the Paul Newman Daytona above, this is a much easier watch to get your hands on. With over 30 years of production, you can expect to find lots of these out in the world, with much more affordable price tags. 

3. Rolex Explorer II (Ref. 1655) 

This watch, often called the “Steve McQueen,” gets a similar level of prestige as the Paul Newman Daytona, due to its association with legendary screen actor Steve McQueen.

It is the younger sibling to the 1016 explorer, with a distinctly orange hand and a chunky dial. Although this was one of the less sought-after watches of its time, it has since become a classic and a great pick for anyone interested in 1970s vintage watches. 


4. Rolex GMT-Master (Ref. 6542)

The GMT-Master range is one of the most iconic series of watches in Rolex’s history.

This specific model is one of the most sought-after for collectors and is well-known for its bakelite materials and blue/red coloring, as well as its cameo in one of the most beloved James Bond movies Goldfinger.

If you’re looking for something that is right out of the 1950s, this is a great piece to go for. You should know that there aren’t many of these left, and if you want to pick one up you should expect to go for anything over $100,000. 

5. Rolex Gmt-Master (Ref. 1675)

The 1675 Rolex GMT-Master is one of the most easily recognizable watches that you can find, but this doesn’t limit its prestige and value.

Although it looks a little more simplistic than the GMT-Master 6542, it features a similar design and can be found in all kinds of different color combinations.

Gold variations are generally the most expensive type, but this is a great choice if you’re looking for something that people will recognize as a Rolex watch without having to look too closely.


6. Rolex Submariner (Ref. 6538) 

This is another Rolex watch heavily associated with James bond. This particular model was featured in several James Bond films, including Dr. No, Goldfinger, Thunderball, and From Russia with Love.

If you’re looking for a gorgeous watch model that will make you feel like Sean Connery, then this is going to be the one for you. The Submariner is arguably the most iconic Rolex Watch of all time, with a noticeably large crown and a revolving pitch-black bezel. 

7. Rolex Submariner (Ref. 5512)

Rolex Submariners were created as a diving watch, and as a result, have been designed to be waterproof. This is a neat little watch with aesthetic blue components and reliable chronometer movement.

Often described as timeless with a noticeable wrist presence, you can expect one of these to be easily recognizable as a Rolex, especially with the blue color combination. 


8. Rolex Datejust (Ref. 1601) 

Next up is a lavish watch that speaks of late dinner dates at impressive places. The Datejust 36 is a range from the 1960s/1970s that is still available for some impressively affordable prices.

A 36mm 1601 is iconic for its white gold and distinctly fluted bezel creating something that is a total classic. For the first non-sport watch on our list, you should take note of the date wheel that will flip over at exactly midnight.

Although vintage Datejust watches have become more sought-after by collectors in recent years, they’re still relatively cheap compared to some of the other iconic watches on our list.


9. Rolex Milgauss (Ref. 6541) 

Back in the 1950s, Rolex created a series of watches that were designed for working individuals.

There’s a big chance you’ve already heard of some of the other watches on this list—Submariner, GMT, or the Explorer—but a lesser known sibling is the Milgauss.

This watch was created for professions such as engineers and/or scientists. 

The Milgauss has a unique feature that makes it suitable to wear around strong magnetic fields.

This is an incredible watch to pick up if you want something that is both vintage and lesser known, however, you should know that these are very rare.

Both the 6541 and the 6543 models were not popular at the time, meaning that there aren’t so many in existence and those that are have become extremely valuable. 


10. Air-King (Ref. 5500)

The Rolex Air King is a great choice for a more decadent Rolex watch. Rolex Air-Kings are lightweight and simplistic, with a basic 3-dial system and an oyster case.

This was a popular watch at the time of its inception, and as a result, you will be able to find it in a whole range of different color combinations. Another great thing about Air-Kings is that they are fairly easy to find, with a price range of $3000 at the lowest. 


11. Rolex Sea-Dweller (Ref. 1665)

The Rolex Sea-Dweller has some of the most intense design details of any watch on this list.

It was created to push the boundaries of what was possible for diving watches, and is able to withstand up to 2000 ft of water resistance.

The record for a dive with this watch happened in October of 1977, when diver Jacques Verpeaux took it on a dive 501 meters below sea level.

Today, these watches are as rare as they are impressive, and an incredible 70s piece of design to own if you can find one. 

Final Thoughts

So that was our list of the 11 best vintage Rolex watches we could find that will enhance your style.

Rolex watches can be pricey and difficult to get ahold of, but each one of them can act as the centerpiece of your outfit that will turn heads and transform simplistic fits into something much more interesting.

Just note that with all of the vintage pieces we mentioned above, there are many different versions of them, as in the past many were custom-made or had custom parts.

We hope that this article has told you everything you needed to know about the best vintage Rolex Watches.

If you still have some questions, make sure to check below for our extensive FAQ that will teach you some additional information about vintage Rolex watches.

We wish you the best of luck on your vintage fashion journey and hope that you find some incredible accessories to complement your outfits! 

Willa Price

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